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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1501763Generated: October 26, 2026

Cesium carbonate → tert-Butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

https://huagongshe.com/reaction/1501763

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
Reactant4-bromo-5H-furan-2-oneHCID 11789536—
Reactanttert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylateHCID 49760149—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Producttert-Butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylateHCID 86709452—

Reaction Conditions

Temperature90 °C

Reaction Steps

A microwave vial was charged with commercially available tert-butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate (Shanghai AQ BioPharma Co., Ltd, catalog #ABP3640, 100 mg, 0.373 mmol), 4-bromofuran-2(5H)-one (72.9 mg, 0.447 mmol), Pd2(dba)3 (17.06 mg, 0.019 mmol), Xantphos (32.3 mg, 0.056 mmol), and cesium carbonate (182 mg, 0.559 mmol). The vial was sealed, degassed, and filled with toluene (1.5 mL). The reaction mixture was heated at 90° C. overnight, and was filtered through CELITE®. The filtrate was evaporated to give the crude product, which was purified by column chromatograph (0-10% MeOH/DCM) to afford the title compound. LC/MS: [(M+1−56)]+=295

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09206198B2
Source datasetuspto-grants-2015_12
ORD IDord-a1fa190dc1d24657992d585df76418cb
Source noteuspto-grants-2015_12